Optimisation of reaction conditions ab.
| ||
|---|---|---|
| Entry | Change from conditions above | 3a (%) |
| 1 | None | 54% |
| 2 | Addition of 5 eq. pyridine | 55% |
| 3 | Addition of 5 eq. 2,6-lutidine | 53% |
| 4 | 30 mol% 1 | 55% |
| 5 | 20 mol% TEMPO in place of 1 | 52% |
| 6 | No 1 added | 25% |
| 7 | 10 mA | —c |
| 8 | No current | 0% |
| 9 | 0.1 M [TBA][PF6] in place of LiClO4 | 20% |
| 10 | 0.1 M [TBA][BF4] in place of LiClO4 | 13% |
| 11 | 0.1 M [TBA][ClO4] in place of LiClO4 | 21% |
| 12 | 0.1 M NaClO4 in place of LiClO4 | 42% |
| 13 | 0.5 mmol 2a and reaction time of 3 h | 43% |
| 14 | 0.5 mmol 2a and reaction time of 6 h | 98% |
| 15 | 2 mmol 2a and reaction time of 24 h | 99% |
| 16 | 0.5 mmol 2a, 3h, Pt anode, Ni cathode | 46% |
| 17 | 0.5 mmol 2a, 3h, glassy carbon anode, Ni cathode | 41% |
| 18 | 0.5 mmol 2a, 3h, graphite anode, Pt cathode | 35% |
Reactions performed on the 1 mmol scale unless stated otherwise.
Product conversion determined by 1H-NMR spectroscopy.
Significant electrode fouling observed.